
Shelter Island Vacations from ₩1,498,242
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Shelter Island Vacation Packages

Nova Hotel Brooklyn
Reviewed on Mar 17, 2026

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder
Reviewed on Mar 22, 2026

The Fifth Avenue Hotel
Reviewed on Mar 1, 2026
Where to stay in Shelter Island

Silver Beach
While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.
Find the Best Shelter Island Vacation Packages
Shelter Island Beach Vacation
There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa
The food was delicious. There was an issue with the pool which will be fixed soon. My big complaint was room location. I am a senior citizen and my room was in the 700's. Many steep stairs to get down to main building. They offered a ride from my room to main building which I had to use because it ...
Reviewed on Mar 21, 2026

Montauk Manor
Great property
Reviewed on Mar 19, 2026

Water's Edge Resort & Spa
Easy
Reviewed on Mar 21, 2026
Discover the most popular places to visit in Shelter Island
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.





